Chlorine → Ethyl 4-chloro-5-ethylsulfonylamino-2-fluorocarbanilate

HRID 36800Notes

Reaction equation

HRID 36800 reaction equation
[CH2:1]([S:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([F:19])=[C:11]([CH:18]=1)[NH:12][C:13](=[O:17])[O:14][CH2:15][CH3:16])(=[O:5])=[O:4])[CH3:2].[Cl:20]Cl>O1CCOCC1.O>[Cl:20][C:8]1[C:7]([NH:6][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:18][C:11]([NH:12][C:13](=[O:17])[O:14][CH2:15][CH3:16])=[C:10]([F:19])[CH:9]=1

Participants

5

Reactant 2

HCID 24526ChlorineHCID 10891582Carbamic acid, [5-[(ethylsulfonyl)amino]-2-fluorophenyl]-, ethyl ester

Product 1

HCID 10903456Ethyl 4-chloro-5-ethylsulfonylamino-2-fluorocarbanilateYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

0.50 g (1.72 mmol) of ethyl 5-ethylsulfonylamino-2-fluorocarbanilate was dissolved in a mixture of 5 ml of dioxane and 1 ml of water, and chlorine gas was added to the resultant solution at a temperature of not higher than 25° C. until the starting material disappeared. After the reaction was completed, the surplus chlorine gas was removed by blowing nitrogen gas thereinto, and water was added. The precipitates crystals were filtered out and dried to obtain 0.48 g of the objective product (yield: 86%) in the form of light brown crystals.

Workup

  1. customthe surplus chlorine gas was removed
  2. additionwater was added
  3. filtrationThe precipitates crystals were filtered out
  4. customdried

Sources & evidence

ORD record
ord-37eb7b14a6974094b8b91fc26352c817
Source dataset
uspto-grants-1995_05
Patent number
US05416236

Reaction notes

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